So here's my dilemma. I can do either of the following: Convert my ALAC music to 256 kbps and store all of it on my iPhone, before outputting directly to my headphones. Use my iPhone as a remote for my iMac's iTunes, and direct the sound to my 2nd Generation Apple TV, before outputting the signal through optical to my headphones. Now, I have my doubts concerning the quality of the Optical Out of the Apple TV: will I be losing quality if I use it ? Furthermore, will AirPlay degrade the quality of my lossless audio ? In any event, my question is the following: is it worth putting the second system highlighted above into effect sound quality wise ? I think AirPlay is a bit-perfect way to stream audio, but I could be wrong, and in that situation, the iPhone might simply be a better solution. Thanks in advance ! EDIT: would I also be losing quality using a converter to change the optical out of the Apple TV into a standard 3.5mm female port for my headphones ?